IP Library Granted Patent US 11,014,870
Granted Patent B2
US 11,014,870 · App. 16/405,523 · Granted May 25, 2021

Procedure for the preparation of 4-phenyl butyrate and uses thereof

Inventors: Huai-Chueh Chang (Tower Lakes, IL); Steven S. Pfeiffer (Camarillo, CA); Vasilios H. Iskos (Chicago, IL); Maki Uragami (Bethlehem, PA); Steven Weissman (Short Hills, NJ); Andrew Thompson (Mountainside, NJ)
Assignee: Horizon Therapeutics, LLC
C07C69/616C07C51/29C07C51/60C07C57/30C07C67/14
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Quick Facts
Patent No.
US 11,014,870
App. No.
16/405,523
Granted
May 25, 2021
Kind
B2
Abstract

Provided is a process for preparing 4-phenyl-1-butyric acid, comprising: reacting 4-phenyl-1-butanol with sodium chlorite, a nitroxyl radical catalyst and sodium hypochlorite in an organic solvent and a phosphate buffer; and quenching the reaction with sodium sulfite to produce 4-phenyl-1-butyric. Also provided is 4-phenyl-1-butyric acid prepared by such a process.

Claims (6)

1. A composition comprising 4-phenyl-1-butyric acid and less than 0.04% 3-benzoyl propionic acid w/w as measured by area percentage of HPLC.

2. The composition of claim 1 , wherein the 4-phenyl-1-butyric acid is prepared by a process comprising:

reacting 4-phenyl-1-butanol with sodium chlorite, a nitroxyl radical catalyst and sodium hypochlorite in an organic solvent and a phosphate buffer; and quenching the reaction with sodium sulfite.

3. The composition of claim 1 , wherein the 4-phenyl-1-butyric acid is greater than about 90% pure by weight.

4. The composition of claim 1 , wherein the 4-phenyl-1-butyric acid is greater than about 90% pure by high performance liquid chromatography (HPLC) analysis.

5. The composition of claim 1 , wherein the 4-phenyl-1-butyric acid has a melting point of 52° C. as determined by differential scanning calorimetry (DSC) analysis.

Assignments (4)
MERGER AND CHANGE OF NAME Recorded Dec 21, 2023
From: HORIZON THERAPEUTICS, LLC; HORIZON ORPHAN LLC
To: HORIZON THERAPEUTICS U.S. HOLDING LLC
Reel/Frame 065928/0608 →
RELEASE OF SECURITY INTEREST Recorded Oct 6, 2023
From: CITIBANK, N.A.
To: HORIZON THERAPEUTICS U.S. HOLDING LLC (FKA HORIZON ORPHAN LLC); HZNP LIMITED; HORIZON THERAPEUTICS U.S. HOLDING LLC (SUCCESSOR IN INTEREST TO HORIZON THERAPEUTICS, LLC)
Reel/Frame 065154/0041 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 26, 2021
From: CHANG, HUAI-CHUEH; PFEIFFER, STEVEN S.; ISKOS, VASILIOS H.; URAGAMI, MAKI; WEISSMAN, STEVEN; THOMPSON, ANDREW
To: HORIZON THERAPEUTICS, LLC
Reel/Frame 056362/0188 →
SECURITY AGREEMENT Recorded Aug 17, 2020
From: HORIZON ORPHAN LLC; HORIZON THERAPEUTICS, LLC; HZNP LIMITED
To: CITIBANK, N.A.
Reel/Frame 053515/0273 →